


Try and Try Again

by perksofbeinganangel



Category: Supernatural
Genre: F/M, M/M
Language: English
Status: In-Progress
Published: 2014-05-30
Updated: 2014-05-30
Packaged: 2018-01-27 14:30:16
Rating: Teen And Up Audiences
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 2
Words: 4,212
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/1713986
Author URL: https://archiveofourown.org/users/perksofbeinganangel/pseuds/perksofbeinganangel
Summary: <blockquote class="userstuff">
              <p>After the fall Castiel struggles to be human and cope with these new feelings, Dean struggles with his emotions for the ex-angel and Sam struggles to cope with the two lovesick idiots who refuse to admit how the feel to one another. With a little intrusion from Charlie maybe they could both figure out just how much they actually mean to one another.</p>
            </blockquote>





	1. Chapter 1

**Author's Note:**

> My very first full length fic, not sure how often I will update it but hopefully it will be every week. Thanks for reading :-)

It was a rainy Saturday afternoon when Dean got the phone call, grumbling about how it had disrupted the movie before getting up from the couch and walking into the kitchen, grabbing the phone along the way. He spoke in a hushed voice when he realised who it was, preferring to keep the whole thing a surprise, at least for now.  
"So when are you due to arrive?" he asked in a quiet voice down the phone as he paced the kitchen, looking for something to eat.  
"I'll be in town in about four hours, I've got to swing by the store before I come to the bunker but expect me before it gets dark," the female on the other end of the line responded chirpily before the line went dead and Dean was left in silence once more. He rooted through the cupboards, pulling out various bags of things such as marshmallows, more buttered popcorn and some crisps that Cas really enjoyed. He sauntered back into the living room, tossing the marshmallow bag in the general direction of Sam and Kevin who were sprawled out across the bigger of the two couches. The pair both made a grab for it but Sam got there first, pushing Kevin back with his huge bear-like hands and knocking the younger boy back down before claiming the marshmallow bag for himself.  
"Sammy, you better share that, kid needs it more than you do," Dean scolded, trying to sound serious but only just managing to hide a smile. The older Winchester moved around the coffee table and dropped the bag of crisps neatly in Cas' lap before plopping down on the sofa beside the fallen angel.  
"I don't understand this Dean-" Cas began but Dean shushed him quickly, rolling his eyes the other man as if Star Wars was the most simple thing for an ex-angel to understand. "But Dean I-" he mumbled in protest but was quickly shushed again when Dean hurled a piece of popcorn at the side of his head.  
"Just shut up and watch the damn film Cas," he said sternly, turning his head slightly to hide the smirk that had formed when he had seen Cas' reaction to being pelted with popcorn.  
"So who was on the phone?" Sam asked, changing the subject. The younger Winchester had his eyes glued to the screen and was shovelling generous amounts of marshmallows into his mouth batting away Kevin's hands whenever they got anywhere near his precious little snacks.  
"Uh no-one, just another hunter calling about a case in Nebraska," Dean lied, trying to look distracted by the movie and ignore the squinty eyes that Cas was now giving him.  
"It didn't sound like a hu-" Cas began again, his voice suspicious as he tilted his head at Dean but was quickly stopped again by another piece of popcorn hitting him square between the eyes.  
"Shut up Cas," Dean growled, turning back to the screen and scowling at it until he was sure Cas had finally looked away. Cas grumbled to himself but turned his eyes back to the screen, squinting at that instead as if he were trying to figure it out. "Problem Cas?" Dean asked when Cas' confused looks which were now accompanied by curious little sounds got too much to bear. Apparently Sam and Kevin hadn't noticed as the pair were still silently bickering about marshmallows and now the couch, it seemed Sam was way too big to share and Kevin was being awkwardly pushed off, slowly but surely.  
"It's just I do not understand how Luke could be so oblivious, Darth Vader is clearly his father as the name itself says 'Dark Father'," Cas explained, causing Dean to roll his eyes. Of course Cas would guess the biggest plot twist of them all without even trying.  
"Look Cas, just be quiet, much on your crisps and enjoy the film, okay?" Dean said, putting on a small little smile to convince Cas that this was a good idea. The fallen angel nodded and crossed his legs up onto the couch before carrying on with his crisps, his eyes fixed attentively on the screen. Dean smiled slightly, more sincere this time before pulling his own legs up onto the couch, shovelling some more popcorn into his mouth and trying to avoid thinking about the way that his toes were brushing the side of Cas' leg. Cas managed to keep silent for the rest of the movie, occasionally shifting to get comfy again but then settling back down, further into the couch. The credits rolled and Dean felt the need to applaud like he usually did at the end of a classic sci-fi movie causing Sam to huff and roll his eyes before taking the DVD out of the player. Kevin just chuckled at the pair's antics before grabbing the discarded bag of marshmallows from where Sam had dropped them before he came back and claimed them again. Dean let out a bark of laughter at the mock look of anger that Sam shot Kevin as he put the DVD away, placing the case back in the box that was labelled 'Dean's Movies'. Dean was hauling himself up from the couch, holding the empty bag of popcorn that he had scoffed in one hand whilst supporting his muscular frame on the arm of the couch with his other, when he spotted Cas also had an empty bag of crisps. "Want me to take that to the bin for you Cas?" he offered, shocking the other man out of his own little world.  
"Oh... yes thank you Dean," Cas said gratefully, passing his crisp packet to Dean with a small smile tilting up the corners of his lips. Dean crumpled the empty bag up in his other hand, passing behind the back of the couch on his way to the kitchen and ruffling one hand through Cas' unruly mop of raven black hair. He ignored the sound of cracking whips from Sam and Kevin that followed his exit, leaving them to deal with Cas' questions as to why they were pretending to have whips and crack them at Dean.  
Dean binned the two empty packets before hunting around for a clean glass, grumbling to himself about the fact that it was Kevin's turn to wash the dishes. He finally found one, placing it on the side before wandering over to the fridge and pulling out the orange and mango smoothie that was currently Cas' favourite. He grabbed three chilled beers before closing the fridge door and wandering back over to the empty glass, skilfully balancing the three bottles and carton of fruit smoothie in his arms. He dropped them on the countertop before pouring the smoothie into the glass and binning the empty packaging. He carried the four drinks back into the living room, tossing a bottle of beer to Sam and Kevin before passing Cas his smoothie and dropping down onto the couch again with a heavy sigh.  
"Dean what does whipped mean, Sam and Kevin won't tell me," Cas moaned, his voice almost like a young toddler who wasn't getting his own way. Dean shot a glare at Sam who was sniggering along with Kevin, both of them obviously amused by Cas' usual obliviousness.  
"Nothing Cas, it doesn't matter. They're being mean again," Dean confirmed before scowling at the pair of them. He wasn't annoyed at them for teasing him, he was annoyed that they had teased Cas because when you teased Cas it was like teasing a little kid, it just wasn't fair. He didn't even understand half of what they said anyway. Kevin began channel surfing before settling on a documentary about penguins that Sam had insisted that they watch, ignoring the groans that came from Dean. They all settled down once more in the dark living room, eyes fixed on the TV as they gradually before more comfortable in their positions, Kevin climbing onto the small armchair ,that wasn't normally used, so he could spread his legs a little more and not be blocked by Dean's human/giant brother. Cas gulped down his smoothie before placing the glass on a coaster on the coffee table before curling up on the couch again, placing his head in Dean's lap like he would usually do on a movie night when he got tired. Dean tried very hard to ignore the fact that his fingers were now carding through Cas' dark hair, brushing it out and massaging his scalp with gentle fingers. He also ignored the pointed looks that Sam and Kevin were giving him as they mimed flicking whips once more. Soon enough Kevin had passed out, much like Mr. Comatose who was now drooling in Dean's lap as he let out little snores every so often. Sam looked like he was on the brink of exhaustion, his eyes drooping lazily every so often until he jolted himself awake once more and pretended to be completely absorbed in the penguin documentary.  
"Just go to sleep man, you look like hell," Dean remarked when Sam jolted awake for what seemed like the millionth time that evening.  
"Wow, thanks Dean," Sam chuckled but let out a contented sigh before laying his head back on the arm of the couch, closing his eyes. His snores followed just minutes later, making Dean laugh to himself. He was about halfway through the documentary when he saw his phone light up, a text from Charlie saying she was outside. Slowly, Dean removed Cas from his lap, being very careful not to wake the other man and laying him back down on the couch before creeping to the front door of the bunker, unlocking everything and opening it up. He swung it open on it's creaking hinges to reveal a red-headed girl who was grinning from ear to ear, surrounded by a few rather large duffel bags.  
"Miss me?" she smiled before launching herself at Dean, glad when he wrapped his arms around her and spun her around in a huge, bear-hug.  
"Charlie, it's good to hear your voice again. How you been?" he asked after releasing her and grabbing most of her bags to help cart them inside, making sure to lock the front door after himself.  
"Oh it's been a good few months, I've not had any run ins with monsters and I've actually started dating one of the girls I LARP with," she smiled, keeping her voice quiet when she spotted the three sleeping forms in the living room.  
"I'd have told them to wait up but frankly they were all exhausted," Dean apologised when he realised Cas had spotted the sleeping trio.  
"That's fine, it was a long drive and I think I could do with some rest. Would you care to take me to my sleeping quarters good sir?" she said in an overly posh voice, a small grin on her lips as she offered her arm to Dean.  
"Why of course fair maiden," Dean responded, taking Charlie's arm and leading her down the hallway towards one of the guest rooms, bags still balanced in his other arm.  
She settled in right away, beginning to unpack almost as soon as the bags had been dumped on the bed with a grumble of effort from Dean. "If you need anything, my room is down the hall and Sammy's is just opposite yours and to the left," he instructed, smiling at her.  
"Okay," she smiled, placing some of her clothes into the drawers whilst she spoke, "and if I hear any strange sounds from your's and your boyfriend's room I will not be amused, Dean."  
Dean glared at her with mock anger, there she was, the annoying little sister that he never wanted. "He isn't my boyfriend Charlie, I'm pretty sure he doesn't like anyone like that, period," Dean sighed, rubbing the back of his neck awkwardly. "Listen, I'm going to go and turn everything off, I'll see you in the morning," he smiled before turning around and walking out of her room, closing the door firmly behind him. As if it wasn't enough with Kevin and Sam teasing him non-stop, now he had Charlie who would most likely want to play match-maker the whole time that she was here.  
"Dean?" the small voice interrupted him from his jumble of thoughts and it took a second to locate it. He was surprised when he spotted Cas sat up on the sofa, normally when he fell asleep there was no waking him. "Are you okay Dean? What's wrong?" he asked, nervously, obviously thinking that something had happened seeing as Dean had moved from the couch.  
"Nothing, Charlie got here about ten minutes ago, I just helped carry her stuff in," he explained as he turned off the TV that was playing to itself. "Come on, let's get you back to your own bed, may as well now that you're up," Dean sighed as he hauled Cas off of the couch, supporting the other man's frame with his arms.  
Now it was no secret that Dean often opened up his room to Cas, especially just after the fall when the ex-angel's nightmares were filled with images of burned up wings. He wouldn't admit to anyone that he enjoyed waking up to find Cas beside him and despite the fact that they would never touch in an intimate way, it still felt nice for Dean. So it was no surprise when the pair mindlessly headed for Dean's room instead of Cas' that was hardly used anymore. Dean helped Cas down onto the bed before grabbing his pyjama shirt and headed to his own side of the bed, turning his back on Cas so that the other man could get changed in some privacy. Dean shucked off his own jeans and plaid shirt, leaving him in just a pair of boxers and his usual plain blue shirt.  
"You can turn around and get in now," Cas chuckled, climbing into his own side of the bed with a sigh. The bed groaned when Dean climbed in and shifted around a little to get comfy, settling finally on facing Cas, his body curled around the other man, just barely touching him. There was hardly any contact at all until Cas rolled over, tucking his head against Dean's chest and wrapping one arm around the elder Winchester's waist as if to reassure himself that he wasn't going to leave him alone. "G'night Dean," he mumbled as he let out a yawn, nestling his nose even further against Dean's chest and closing his eyes.  
"Night Cas," he replied, his lips tilting up in a small smile just before he succumbed to sleep.


	2. Chapter 2

Charlie was the first one up that morning, making her way down the hallway and back into the living room area. Dean and Cas were awake next when they heard Sam shouting something from the living room, his words a mix of threats and insults which were most likely being hurled at Charlie.  
"I'll go and put some coffee on," Dean said awkwardly, pulling away from Cas' grasp around his waist and clambering out of bed. He grabbed his dressing gown from the door and pulled it on, tying it around his waist before making his way to the living room to find out what the whole fuss was.  
When he rounded the corner he burst out laughing at the sight, Charlie had Sam pinned down and Kevin was struggling with her, trying to pull her off of the younger Winchester. "Hey! Hey, get off of her, break it up guys," Dean shouted as he made his way over and hauled Kevin away from Charlie before pulling Charlie off of Sam, ignoring the girl's protests.  
"Dude, when did Charlie get here and why did she just attack me," Sam grumbled at Dean, shooting a glare at Charlie who rolled her eyes.  
"I did not attack you, it was just a friendly wake-up call," she smiled causing Sam to lunge for her again, obviously annoyed at being woken up.  
"Okay okay, break it up you two. Charlie got here last night, she called to tell me she was coming to stay here for a while. Kevin this is Charlie, Charlie this is Kevin, he's a prophet," Dean explained, doing the introductions before he made his way towards the kitchen. "I'm putting some coffee on, anyone else want some?" he asked as he stood in the doorway.  
"Me!" Charlie and Sam shouted at the same time, just as Cas rounded the corner, still looking very sleepy. His hair was sticking up at odd angles and he was now wearing one of Dean's old shirts that was way too big for him and his own boxers.  
"Morning sleepy," Dean grinned at him, feeling his stomach lurch with butterflies at the sight of Cas like this.  
"Put me down for coffee," he shot back as he walked over to the couch and flopped down on it just as Dean left the room to sort out drinks.  
"So you're the famous Cas, I've heard so much about you!" Charlie said enthusiastically as she plopped down on the couch beside Cas, a grin from ear to ear. "All good things of course, Dean tells me you're learning about humanity very quickly, adapting well," Charlie smiled at him.  
"Dean talks about me?" Cas asked shyly, his cheeks flushing bright red as he spoke which made Charlie giggling with delight.  
"Yeah, only all the ti-" Charli began but was interrupted when Dean wandered back in with the four cups of coffee.  
"That's a lie and you know it Charlie," Dean said, his voice warning. He didn't want Charlie to give away his big, gay secret thing that he currently had going on. Charlie noted the sadness in Cas' eyes as he looked up at Dean when he got handed his cup of coffee. She also noted the fact that Dean sat down on the smaller couch with her and Cas even though there was plenty more room on the bigger one.  
"So what have you guys been doing without me?" she asked, changing the subject in the hopes of making Dean and Cas a little more comfortable again.  
"We hunted a Rugaru, few weeks back in Minnesota but nothing much, we're basically waiting around for the war in hell to stop and for someone to take Metatron out," Sam explained as he sipped at his scalding hot coffee, making a face at the bitter taste of it.  
"Yeah, like someone is going to off that dick-bag for us," Dean scoffed as he drunk his own coffee, grumbling something to himself.  
"You never know, he is sort of hated by every angel out there at the minute," Cas interjected, looking over the top of his own mug, a little more perky than before. "There's no telling who wants him dead," he said simply, looking down again.  
"Well now you guys are all on a break from saving the world we can afford to chill out right?" Charlie grinned, looking around the unenthusiastic group. "I'm thinking karaoke, pizza and beers tonight?" Charlie offered which Kevin and Sam agreed to.  
"Pizza and beer sounds good but you can think again if you reckon I'm going to sing," Dean grumbled, looking up at Charlie and pretending to be annoyed with her plans.  
"Great! So now that tonight is organised what are we going to do today?" she giggled, crossing her legs up onto the couch.  
"Well me and Dean have research to do, you could take Cas for a run into town and stock up on supplies?" Sam offered hopefully.  
"Sure thing, me and Cas can handle that right?" she said loudly, throwing an arm around the dark haired man who looked around with a bewildered expression upon his face.  
"Uh yes, I think.." he stammered after a little while, relaxing against Charlie's arm that was still slung over his shoulder. Charlie did notice the pissy look Dean was now giving her, probably because she was touching his precious little boyfriend but she was having way to much fun to care about that.  
"Okay, list is on the side, don't even think about trying to corrupt Cas," Dean said simply before standing up and stretching out his arms and legs. "I'm going to go and get a start on the reading," he grumbled before stalking away and down to hall to what Cas assumed must be the Men of Letters library.  
"Okay Cas, go and get changed into something that isn't Dean's and we can go shopping," she grinned, bouncing up off of the couch and flouncing off to her room, presumably to change into something else. Cas sat staring at Sam and Kevin with a terrified look on his face, clearly wondering what exactly he had gotten himself into.  
When Cas had finally finished off his coffee and gotten changed into something a little more fitting, leaving Dean's shirt on the other man's bed, he wandered back into the living room to find Charlie playing Mario cart with Kevin. She smiled up at Cas, stopping the game and promising Kevin a rematch later before getting to her feet and grabbing her bag. Cas got the shopping list and they were off, climbing the stairs to the front door and exiting the bunker, locking it behind them. Charlie had parked her car a short while up the road so they walked until they found the little yellow thing that Dean would've scoffed at had he seen it. "So, we need to get everything on the list, plus a rocking outfit for you so you can catch Dean's eye," Charlie blurted out, a small grin on her lips as she climbed into the driver's side of the car.  
"I don't understand, why would I want to catch Dean's eye," Cas responded, completely oblivious to anything Charlie was trying to imply. He clambered into the car after her, buckling up his seatbelt and waiting for Charlie to start the ignition.  
"You do like Dean right? Not just as friends but in a more...romantic way?" she asked curiously, already guessing what the answer would be. Cas just flushed bright red and hid his face from her, covering it up with his hands.  
"Maybe...just a little but he doesn't care, Dean likes girls and I do not think I am a girl," Cas grumbled into his hands causing Charlie to let out a burst of laughter.  
"Jesus, you two need to open up your eyes a little, you're dancing around each other like a pair of love-struck colts," Charlie chuckled, clapping Cas on the shoulder in a friendly manner.  
"I do not think Dean is attracted to me Charlie, end of conversation," Cas said, his face finally returning to it's normal colour at he shot Charlie a sad look.  
"Either way, you need new clothes," she smiled, starting up the car and pulling out before turning the car around and heading towards the local town.  
The drive was silent, save for Charlie's ridiculous pop music that was blasting from the speakers right until the moment they rolled into town and Charlie found them a parking space next to the supermarket. They both climbed out of the car, locking it up behind them, before Charlie explained that she would go and buy things from the shopping list and Cas should go straight ahead to the clothes store to pick out some things. Cas agreed half-heartedly before trudging off in the opposite direction of Charlie, making his was as slowly as humanly possible to the clothes shop. He walked through the automatic doors and was surprised when he found the store mostly empty of people aside from the workers. A nice lady named 'Matilda' came bouncing over to Cas and immediately started leading him around the men's aisles, asking him what he was looking for and what he liked. He ended up piled with shirts and trousers and jackets galore and then Matilda was ushering him into the changing room, telling him to put something on and see how he liked it. Cas did as he was told, trying on several different things that included various plaid shirts, lot's of skinny jeans that he was very fond of and a few dress shirts and ties but in the end he decided to get: a red and dark blue plaid shirt, two pairs of plain black skinny jeans, a blue dress shirt and a thin black tie to match. He exited the little booth and passed the unwanted clothes to Matilda who hurried off with them, probably to return them to where they had gotten them from, Cas assumed. Cas paid for his items with a credit card that Sam had given him and had them bagged up before he strolled out of the store, just in time to see Charlie come bounding around the corner, bags of items in hand. They loaded everything up into the car, Charlie nodding in approval at the clothes that Cas had purchased before closing the boot and getting into the driver's side, buckling up and checking Cas was strapped in before starting up the car and heading back to the bunker.


End file.
